We Could've Had It All
by olicityplease
Summary: Olicity - AU. A different way Oliver and Felicity could've met and fell in love.
1. Chapter 1

Oliver Queen had been back from the island for two years the first time he met Felicity Smoak. With both of his parents dead – his father from suicide to save Oliver and his mother from cancer – he finally took his "rightful place" as CEO of Queen Consolidated. To say he did it reluctantly would be putting it nicely. Walter, his father's ex-CFO and mother's widower, swore this was what his parents would have wanted but Oliver doubted that. They wanted their legacy to be a successful corporation and all Oliver would do was run it into the ground. As he had said many times since coming back from the island, he didn't get a business degree while he was away. Yet, here he was. Sitting in an office that felt an awful lot like trying to fill a shoe that would always feel too big.

Oliver had been going over stock numbers and business agreements for so long that eventually it all started jumbling together. He looked at his watch to find it was past seven and he hadn't had dinner yet. The moment the thought of a burger from Big Belly Burger entered his mind, his stomach growled. He threw his pen down in frustration and stood up, deciding this could all be finished tomorrow. He grabbed his suit jacket, not bothering to put it on, and headed for the elevator.

On the way down, the elevator stopped at the 23rd floor to let someone on. Oliver had been staring at his phone and when the doors closed, he was just going to keep seeing what the tabloids had said about him recently when the woman on the elevator with him gasped. He looked up and he felt like the breath had been knocked out of him.

In front of him stood the most beautiful woman he had ever seen in his life. She had blonde hair that looked so soft he wanted to run his fingers through it. And that was with it tied into a ponytail. He decided right then he wanted to see what her hair looked like cascading around her shoulders. She had black rimmed glasses that somehow made her even more beautiful, even though they hid the gorgeous blue eyes that were currently taking him in as well. He smiled at the thought that they were checking each other out simultaneously. His eyes then moved to her lips, which were covered in bring pink lipstick that didn't make her look cheap or like she was trying too hard. He wondered if she just liked the brightness of it in this gloomy building.

"How'd you know?" He heard her say, and he saw her gawking at him.

"Sorry, what?" He replied after a few moments, trying to catch his bearings.

She laughed and said, "You said I wear my lipstick because the building is gloomy. I was wondering how you knew that."

Oliver sheepishly pulled his eyes from hers and stared at his shiny shoes, feeling a blush creep up his neck and make its way to his cheeks. He wasn't sure what to say so he just stayed silent, staring at his shoes for the rest of the ride down the elevator. He had never reacted to a woman like this before. He never had a problem with being charming with women to get them into bed, but this woman was affecting him and he wasn't sure how he felt about it. What was happening to him?

The elevator dinged to signify their arrival to the parking garage and they both went to move at the same time. They both said, "You go first, I insist" at the same time and Oliver couldn't help the grin that formed on his face. He couldn't remember the last time he had smiled a real, true smile and he had to admit to himself that it was nice.

Although, it was short lived.

"Sorry, Mr. Queen. I didn't mean to, uh, get in the way." The young woman said, looking like she was starting to shake. Oliver's smile vanished and he wondered why she was apologizing when it was his fault just as much as hers. And it happened in elevators all the time, so she had no reason to be sorry. He said as much.

"You have no reason to apologize. It was my fault." He told her sincerely. "Ladies first." He continued, making a sweeping gesture of his hand. She smiled shyly and stepped out of the elevator, heading in the same direction Oliver's car was parked. He followed, leaving a few feet between them so he could appreciate her body. She was short, probably 5'5", and her legs were to die for. The dress she was wearing was modest and went to right above her knees, but what he could see of her legs only made him want to see more.

He shook his head to clear his thoughts of taking her against the wall in the parking garage and continued walking. They walked in silence, only the sound of her high heels – was she trying to kill him? – echoing around them.

"Shit." Oliver heard her say, dragging his eyes from her legs to her face to notice that she was digging through her purse. She had stopped about four feet ahead of him to dig through her purse and Oliver found himself wanting to make sure she was okay.

"Hey, are you okay?" He asked her as he reached her side, trying to get a sense of what was going on. She had things falling out of her purse onto the concrete ground and she seemed frantic. She basically had emptied her purse before she noticed he was there and jumped, startled.

"Sorry, did you say something?" She asked him, placing her hand over her racing heart.

Oliver bent over to pick up the things she had dropped (a red pen, her QC badge, and lens cleaners) and returned them to her. His fingers barely brushed hers and the heat he felt at the small contact knocked the wind out of him. She moved her hand back so fast that it made him think that maybe, just maybe, she had felt it too.

"I asked if you were okay." He told her after his heart returned to its somewhat normal speed. It was still racing but that had been the normal for the last, oh, five minutes so he just went with it.

She stuffed her items back into her purse and said, "Yeah, fine. I just left my keys in my office." She then turned around and headed back towards the elevator.

Oliver spent two seconds debating on what to do before he followed her and made it into the elevator just as the doors were closing. She raised her eyebrow in a question that silently asked him what the hell he was doing and he said "What? I can't let you go up there alone at night. I'll go with you. It's not a big deal, Mrs…?"

He watched as she internally battled herself before pushing the button for the 23rd floor and said, "It's Miss, actually. But you can call me Felicity. Felicity Smoak."

Oliver smiled to himself, thinking of all the different ways he could say it.


	2. Chapter 2

The elevator ride back to the 23rd floor was silent except for the beeping of numbers from the elevator rising steadily. Oliver felt like an idiot for the excuse he gave her for basically following her for no reason. Sure, he knew it was a straight shot and that there was security in the building, but he felt this overwhelming need to be around her and protect her. So, he followed that instinct.

When they arrived on the right floor and the elevator doors opened, Oliver saw a sign that said 'IT Department' and he smiled. Of course she was a genius.

They made their way down the hall and into a small office. Oliver leaned against the door while Felicity rummaged around her desk, trying to find her keys. She let out a huff of annoyance when she couldn't find them and muttered "And this, Felicity, is why it's important to keep your desk clean. Because the only person to blame here is yourself." Oliver let out a small chuckle that caught her attention. She brought her eyes to his and smiled a genuine smile that took Oliver's breath away. She was breathtaking. "Sorry, I'm not sure where they are. They should be here because I never leave this damn desk, but I can't find them." Felicity told him, sighing in defeat.

Oliver straightened up and made his way over to her desk with the intent of helping her look. Four eyes are better than two, right? The moment Oliver stood next to her in the small space behind her desk, he knew he had been wrong. Very, very wrong. Being this close to her was intoxicating. Her arm was brushing against his arm and he could smell her light perfume. It was like vanilla with a touch of something else, like her natural scent, and that thought sent him further over the edge. Was he crazy for feeling this way about someone he had only known for about five minutes? Probably. Did he care? Nope.

Oliver swallowed the lump that had formed in his throat and used all the willpower he had to push those thoughts into the back of his mind. He didn't want to scare her away by doing something stupid. You know, like swiping his arm across the desk to clear it of its items haphazardly then picking her up and placing her on the desk and having his way with her.

Well, that visual wasn't going to help him regain his focus or control the strain in his pants.

He finally got his attention back to the matter at hand when Felicity fist pumped, keys in hand. She let out the most adorable "Yay!" Oliver had ever heard and then shot him a grateful smile. They made their way out of her office and back to the elevator.

When the elevator opened, Oliver felt disappointed their time together was almost over. He couldn't think of another way to get her number without coming off as her creepy boss. They shuffled into the elevator and reached for the parking garage button at the same time. Oliver smiled at her and she smiled back, both of them removing their hands and muttering apologies. He shrugged it off and pushed the button, starting their decent.

"Thanks for, uh, coming with me. You didn't have to." She told him, tucking a stray strand of hair behind her ear.

Oliver smiled at her and replied, "It wasn't a problem. Really. I was happy to help." Oliver chastised himself considering all he did was stand there and look like an idiot while she was actually looking for her keys. She didn't seem to mind though, considering he saw a faint blush on her cheeks as she turned her head to look back at the front of the elevator.

Oliver just kept thinking to himself that he was being stupid. "_Just ask for her number, already!" _He thought, but he didn't have the nerve. She was this beautiful, intelligent woman and she would see right through him. She deserved better than anything he could offer her. But, what if she was it for him? What if the sparks he felt, she felt too? What if they could be something great if he would just get his head out of his ass and take this leap of faith? What if, what if, what if. It was like a mantra that kept replaying in his head over and over again.

Screw it.

"Hey, Felicity. I was just wondering if-"

Oliver was cut off when the elevator shook, coming to a sudden stop. The lights then went out and emergency lights came on, dimly lighting the small space. Oliver felt Felicity grab on to his arm, clutching him so hard that he felt himself losing circulation. He put his hand over hers and said, "Hey, it's okay. We're gonna be okay. The building probably just lost power or something. They'll get us out."

In the small amount of light that was in the elevator, he saw her release a shuddering breath at the same time her grip on him loosened and looked up at him, terrified. He gave her what he hoped was a reassuring smile and pushed the call button on the elevator to let the operator know people were stuck in there.

After giving the operator their names and locations and being assured they were doing everything they could to get a rescue team to them, Oliver sat on the floor of the elevator, patting the spot next to him. Felicity sat down, crossing her legs under her, and put her arms around herself. He felt her shiver, so he wrapped his jacket around her shoulders. She muttered her thanks and pulled it tighter around her, almost like it was her security blanket.

Oliver had never felt more useless in his life than he did in that moment. He couldn't offer her any reassuring words because he had none. He hated dark spaces probably as much as she did, if not more. Being in the elevator reminded him of his time on the island and the dark nights that he spent alone. Even now, his dreams were filled with the cold, frigid air that reminded him of his time on the island and the darkness that always surrounded him. But he was going to be strong for her through this. He could get through it. He had to.

With that promise to himself, he pushed away the darkness and the fear he felt and focused on the light: Felicity.


	3. Chapter 3

To say Oliver was feeling uncomfortable in the elevator would be a complete and total lie. Being with Felicity in that hot, small, dark elevator should've made him nervous. He should've been worried about the darkness and the small space and the fact that he was basically with a stranger, but he wasn't worried about any of that. What he was worried about, however, was Felicity's heavy breathing. She hadn't moved or spoken since she sat down next to him and he wasn't sure what to do. He knew she was having the normal reaction to this type of situation, but Felicity had a presence about her that calmed him. He couldn't explain it, and even though she seemed to be close to a full-on panic attack, but having her there with him allowed him to not be selfish for once and be there for her.

She made him a better man without even realizing it.

Ten minutes had passed without a word and Oliver couldn't take it anymore. Who knew when anyone would get there to let him out so he knew he had to distract Felicity. He turned his body to face her and took in her state. She had his jacket wrapped around her shoulders, gripping it so tight he could see the white in her knuckles. Her face was red, probably from the heat, and her hair was sticking up in all directions from her ponytail. She looked disheveled, but still beautiful. He knew he had to say something that would take her mind off of the situation that they were in, so that's what he did.

Oliver cleared his throat and blurted out the first thing that came to his mind. "So, come here often?" He felt mortified after the words left his mouth, convinced all he had done was remind her where they were, but her reaction to what he said left him pleasantly surprised. She smiled and looked at him, clearly amused at his choice of words. He smiled back and he felt himself relax again, his shoulders visibly relaxing at the warmth he felt in his heart when she smiled.

"Well, only five days a week. Not too bad. Although, when there's overtime, I'm here Saturday's too. So, that sucks. But I guess more money is always a good thing. It allows me my awesome DVD collection. And I'm going to stop talking in 3… 2… 1." Felicity took a deep breath and looked away from him, an embarrassed flush making its way up to her cheeks.

Oliver had never seen anything cuter than a blushing Felicity Smoak, he decided.

"Why were you here so late?" He asked her, half because he wanted to start a conversation and half because he was genuinely curious why there was no one else on the IT floor.

Felicity tucked a stray strand of hair behind her ear before answering him, seeming shy. "I'm trying to create software for the company's computers to better protect the top secret projects."

"Wow. I wasn't aware we were trying to create better firewalls." Oliver told her, feeling stupid for not knowing what's going on in his own company.

Felicity smiled sheepishly before replying, "That's because you're not. I'm doing it on my own time, after I finish all of my work for the day, of course. I'm hoping to finish it in the next week then present it to… well… you, I guess."

Oliver felt pride swell in his chest that she was so dedicated to her work. He barely knew her, but he could see she was passionate about what she does. "Well, I look forward to it."

Oliver watched as Felicity opened her mouth to reply, but then the elevator came to life and continued its decent towards the garage. He felt disappointed that their time was over, but he knew he would be seeing her again. As they made their way towards their cars for the second time that night, he couldn't help but compare the differences from the time they were out here not half an hour ago. Before, when they were down here, he was behind her and feet away, simply watching her. But now? Now he was next to her and they were chatting about stupid things like how elevators need a generator themselves and that they were never taking the elevator again. They were both laughing as they reached Felicity's car and she dug her keys out of her purse, jokingly dangling them in front of Oliver.

"Well, thank you for coming with me. I appreciate it. You didn't have to." Felicity told him, her eyes meeting his.

"It wasn't a problem at all. Like I said, I'm happy to help." He remembered his words from earlier and laughed at himself at the irony. Same words, bigger meaning. Now, he felt like they were kind of friends, just standing on the precipice of how to continue. Earlier, he felt like once they parted he never would've seen her again.

He liked this situation much better.

"I should go. It's late and I've got to be back here early. I'll, uh, see you around?" She asked him, and he heard the hope in her voice. He recognized in his own when he replied.

"I'll see you around, Felicity."

He turned around and made his way to the car, getting in and turning on the engine. He waited for her to drive off, waving to her through his front windshield. Then he drove home, smiling like he hadn't ever smiled in his life.

For the first time since returning home from the island, he was excited about what was to come. And that was all because of one Felicity Smoak.


End file.
